JP2017513885A5 - - Google Patents
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- JP2017513885A5 JP2017513885A5 JP2016564031A JP2016564031A JP2017513885A5 JP 2017513885 A5 JP2017513885 A5 JP 2017513885A5 JP 2016564031 A JP2016564031 A JP 2016564031A JP 2016564031 A JP2016564031 A JP 2016564031A JP 2017513885 A5 JP2017513885 A5 JP 2017513885A5
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- Prior art keywords
- metal
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- 238000000034 method Methods 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 37
- 229910052751 metal Inorganic materials 0.000 claims description 31
- 239000002184 metal Substances 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052744 lithium Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 9
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000007333 cyanation reaction Methods 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 8
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 claims description 6
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 claims description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
- 102100039856 Histone H1.1 Human genes 0.000 claims description 6
- 101001035402 Homo sapiens Histone H1.1 Proteins 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 6
- 230000009435 amidation Effects 0.000 claims description 6
- 238000007112 amidation reaction Methods 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical group O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 6
- 238000007171 acid catalysis Methods 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical group Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910001507 metal halide Inorganic materials 0.000 claims description 3
- 150000005309 metal halides Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical group CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 3
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical group C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- RLSHRIPJIKJUIR-UHFFFAOYSA-N CCOC(c(cc1)ccc1-c1nnc(C)[s]1)OCC Chemical compound CCOC(c(cc1)ccc1-c1nnc(C)[s]1)OCC RLSHRIPJIKJUIR-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461985400P | 2014-04-28 | 2014-04-28 | |
| US61/985,400 | 2014-04-28 | ||
| PCT/US2015/027647 WO2015167969A1 (en) | 2014-04-28 | 2015-04-24 | Processes and intermediates for the preparation of a pde10 inhibitor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017513885A JP2017513885A (ja) | 2017-06-01 |
| JP2017513885A5 true JP2017513885A5 (show.php) | 2018-06-07 |
| JP6474430B2 JP6474430B2 (ja) | 2019-02-27 |
Family
ID=54359190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016564031A Active JP6474430B2 (ja) | 2014-04-28 | 2015-04-24 | Ｐｄｅ１０阻害剤の調製のための方法および中間体 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US9650368B2 (show.php) |
| EP (1) | EP3137462B1 (show.php) |
| JP (1) | JP6474430B2 (show.php) |
| KR (1) | KR102496552B1 (show.php) |
| CN (1) | CN106459026B (show.php) |
| AU (1) | AU2015253464B2 (show.php) |
| BR (1) | BR112016025287B1 (show.php) |
| CA (1) | CA2946756C (show.php) |
| ES (1) | ES2723437T3 (show.php) |
| IL (1) | IL248585B (show.php) |
| NZ (2) | NZ716494A (show.php) |
| RU (1) | RU2718863C2 (show.php) |
| WO (1) | WO2015167969A1 (show.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX339950B (es) * | 2010-03-12 | 2016-06-20 | Omeros Corp | Inhibidores de fosfodiesterasa 10 (pde10) y composiciones y metodos relacionados. |
| NZ630803A (en) * | 2014-04-28 | 2016-03-31 | Omeros Corp | Optically active pde10 inhibitor |
| JP2018535969A (ja) | 2015-11-04 | 2018-12-06 | オメロス コーポレーション | Ｐｄｅ１０阻害剤の固体状態形態 |
Family Cites Families (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK178590D0 (da) | 1990-07-26 | 1990-07-26 | Novo Nordisk As | 1,4-disubstituerede piperaziner |
| PT100905A (pt) | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
| ES2192192T3 (es) | 1992-12-02 | 2003-10-01 | Pfizer | Dieteres de catecol como inhibidores selectivos de pde iv. |
| DE4323192A1 (de) | 1993-07-10 | 1995-01-12 | Basf Ag | Verfahren zur Herstellung von Homo- und Copolymerisaten von Alk-1-enen |
| DE4325846C1 (de) | 1993-07-31 | 1995-01-19 | Herberts Gmbh | Verwendung von Furan-modifizierten aromatischen Pinakolderivaten als Initiatoren und Furan-modifizierte aromatische Pinakolderivate als solche |
| DE4343286A1 (de) | 1993-12-17 | 1995-06-22 | Hoechst Ag | Heteroaromatische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen |
| DE4409501A1 (de) | 1994-03-19 | 1995-09-21 | Didier Werke Ag | Verschleißfutter eines Schachtofens und Stein hierfür |
| WO1996000218A1 (en) | 1994-06-24 | 1996-01-04 | Euro-Celtique, S.A. | Compounds for and method of inhibiting phosphodiesterase iv |
| US5789434A (en) | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
| TW424087B (en) | 1995-04-06 | 2001-03-01 | Janssen Pharmaceutica Nv | 1,3-dihydro-1-(phenylalkenyl)-2H-imidazol-2-one derivatives |
| TW332201B (en) | 1995-04-06 | 1998-05-21 | Janssen Pharmaceutica Nv | 1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives |
| US6037370A (en) | 1995-06-08 | 2000-03-14 | Vertex Pharmaceuticals Incorporated | Methods and compositions for stimulating neurite growth |
| DE69712042T2 (de) | 1996-01-22 | 2002-10-02 | Fujisawa Pharmaceutical Co., Ltd. | Thiazolylbenzofuranderivate und pharmazeutische zusammensetzungen die sie enthalten |
| AU4015497A (en) | 1996-08-26 | 1998-03-19 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Thiazole derivatives useful as selective inhibitors of pde-iv |
| JPH1087543A (ja) | 1996-09-17 | 1998-04-07 | Chisso Corp | アルコキシベンゼン誘導体、液晶組成物および液晶表示素子 |
| US6548490B1 (en) | 1997-10-28 | 2003-04-15 | Vivus, Inc. | Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction |
| WO1999045914A1 (en) | 1998-03-13 | 1999-09-16 | Maruho Kabushikikaisha | Alkyl amine derivative and local anesthetic agent using the same |
| GB9807354D0 (en) | 1998-04-07 | 1998-06-03 | Glaxo Group Ltd | Antiviral compound |
| SE9804212D0 (sv) | 1998-12-04 | 1998-12-04 | Astra Pharma Prod | Compounds |
| HK1043127B (zh) | 1999-03-12 | 2004-12-24 | 贝林格尔‧英格海姆药物公司 | 作为消炎剂的化合物 |
| US7141593B1 (en) | 1999-06-04 | 2006-11-28 | Abbott Laboratories | Pharmaceutical formulations |
| GB9929552D0 (en) | 1999-12-14 | 2000-02-09 | Proteus Molecular Design | Compounds |
| US6933304B2 (en) | 2000-06-15 | 2005-08-23 | Pharmacia Corporation | Heteroarylalkanoic acids as integrin receptor antagonists |
| US20030032579A1 (en) | 2001-04-20 | 2003-02-13 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
| PL367091A1 (en) | 2001-05-22 | 2005-02-21 | Pfizer Products Inc. | Crystal forms of azithromycin |
| US20050165185A1 (en) * | 2002-04-18 | 2005-07-28 | Spivey Alan C. | Preparation of a conjugated molecule and materials for use therein |
| US6821502B2 (en) | 2002-06-12 | 2004-11-23 | Chevron U.S.A. Inc. | Method of making aluminum-containing zeolite with IFR structure |
| AU2003254481A1 (en) | 2002-07-27 | 2004-02-16 | Astrazeneca Ab | Chemical compounds |
| JP4628789B2 (ja) | 2002-10-08 | 2011-02-09 | ザ スクリプス リサーチ インスティテュート | 脂肪酸アミド加水分解酵素の阻害剤 |
| JP2006509832A (ja) | 2002-10-30 | 2006-03-23 | ニューロ３デー | サイクリックヌクレオチドホスホジエステラーゼ阻害剤、その調製及び使用 |
| TW200410921A (en) | 2002-11-25 | 2004-07-01 | Hoffmann La Roche | Mandelic acid derivatives |
| JP4464280B2 (ja) | 2002-12-06 | 2010-05-19 | 興和株式会社 | エリスロポエチン産生促進剤 |
| CA2507699A1 (en) | 2002-12-20 | 2004-07-15 | Pharmacia Corporation | Heteroarylalkanoic acids as integrin receptor antagonists |
| WO2004071509A1 (ja) | 2003-02-12 | 2004-08-26 | Nippon Chemiphar Co., Ltd. | オリゴデンドロサイト分化促進剤 |
| AU2004232973A1 (en) | 2003-04-18 | 2004-11-04 | Memory Pharmaceuticals Corporation | Pyrazole derivatives as phosphodiesterase 4 inhibitors |
| AR047541A1 (es) | 2004-02-13 | 2006-01-25 | Sandoz Ag | Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas |
| CN1946703A (zh) | 2004-04-20 | 2007-04-11 | 特兰斯泰克制药公司 | 取代的噻唑和嘧啶衍生物作为黑素细胞皮质激素受体调节剂 |
| WO2005110410A2 (en) * | 2004-05-14 | 2005-11-24 | Abbott Laboratories | Kinase inhibitors as therapeutic agents |
| US7351833B2 (en) | 2004-07-23 | 2008-04-01 | Abbott Laboratories | (1S,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate |
| US7449486B2 (en) * | 2004-10-19 | 2008-11-11 | Array Biopharma Inc. | Mitotic kinesin inhibitors and methods of use thereof |
| US8436176B2 (en) | 2004-12-30 | 2013-05-07 | Medicis Pharmaceutical Corporation | Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine |
| RS51385B (sr) | 2005-01-07 | 2011-02-28 | Pfizer Products Inc. | Heteroaromatična jedinjenja hinolina i njihova upotreba kao pde10 inhibitora |
| CN101384183B (zh) | 2005-02-04 | 2012-07-04 | 西诺米克斯公司 | 包含连接有杂芳基部分的化合物及其作为用于食物组合物的新型鲜味调节剂、促味剂和味觉增强剂的应用 |
| EP1871770A1 (en) | 2005-04-22 | 2008-01-02 | Kalypsys, Inc. | Ortho-terphenyl inhibitors of p38 kinase and methods of treating inflammatory disorders |
| UA91546C2 (uk) | 2005-05-03 | 2010-08-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ |
| MY152185A (en) | 2005-06-10 | 2014-08-29 | Novartis Ag | Modified release 1-[(3-hydroxy-adamant-1-ylamino)-acetyl]-pyrrolidine-2(s)-carbonitrile formulation |
| CA2617788A1 (en) | 2005-08-04 | 2007-02-15 | Apogee Biotechnology Corporation | Sphingosine kinase inhibitors and methods of their use |
| ES2375841T3 (es) | 2005-08-29 | 2012-03-06 | Sanofi-Aventis U.S. Llc | Nueva forma cristalina de un derivado de piridazino[4,5-b]indol. |
| US7642246B2 (en) | 2005-09-13 | 2010-01-05 | Sicor Inc. | Pure rocuronium bromide |
| KR101439557B1 (ko) | 2005-11-15 | 2014-09-11 | 오츠카 세이야쿠 가부시키가이샤 | 옥사졸 화합물 및 제약 조성물 |
| JP2009521429A (ja) | 2005-12-23 | 2009-06-04 | アストラゼネカ・アクチエボラーグ | Ｇａｂａ−ｂ受容体モジュレーターとしてのイミダゾール |
| US20090176829A1 (en) | 2006-05-02 | 2009-07-09 | Pfizer Inc | Bicyclic heteroaryl compounds as pde10 inhibitors |
| US20080090834A1 (en) | 2006-07-06 | 2008-04-17 | Pfizer Inc | Selective azole pde10a inhibitor compounds |
| CA2662535A1 (en) | 2006-09-08 | 2008-03-13 | Ore Pharmaceuticals Inc. | Method for reducing or alleviating inflammation in the digestive tract |
| WO2008039431A2 (en) | 2006-09-25 | 2008-04-03 | Ptc Therapeutics, Inc. | Crystalline forms of 3-[5-(2-fhjorophenyl)-[1,2,4]oxadiazol-3-yl]-benzoic acid |
| CN101528212A (zh) | 2006-09-28 | 2009-09-09 | 默克公司 | Hdac抑制剂和可螯合的金属化合物的药物组合物以及金属-hdac抑制剂螯合物 |
| US20090253918A1 (en) | 2006-10-02 | 2009-10-08 | Janssen Pharmaceuticals, N.V. | Novel intermediate for glyt1 inhibitor |
| US7837978B2 (en) | 2006-10-13 | 2010-11-23 | Chevron U.S.A. Inc. | Process for preparing aluminum-containing molecular sieve SSZ-26 |
| US7786139B2 (en) * | 2006-11-21 | 2010-08-31 | Omeros Corporation | PDE10 inhibitors and related compositions and methods |
| WO2008064342A2 (en) * | 2006-11-21 | 2008-05-29 | Omeros Corporation | Pde10 inhibitors and related compositions and methods |
| PE20081506A1 (es) | 2006-12-12 | 2008-12-09 | Infinity Discovery Inc | Formulaciones de ansamicina |
| WO2009008906A2 (en) | 2007-02-06 | 2009-01-15 | The Trustees Of The University Of Pennsylvania | Therapeutic compounds for blocking dna synthesis of pox viruses |
| EP2160394A1 (en) | 2007-05-22 | 2010-03-10 | Ultimorphix Technologies B.v. | Tenofovir disoproxil hemi-fumaric acid co-crystal |
| EP2017264A1 (de) | 2007-07-16 | 2009-01-21 | Bayer Cropscience Ag | Substituierte Phenylpropargylverbindungen, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| US20090186014A1 (en) | 2007-10-10 | 2009-07-23 | Ore Pharmaceuticals Inc. | Method for treatment of pancreatitis |
| TW200944520A (en) | 2008-01-29 | 2009-11-01 | Glaxo Group Ltd | Spiro compounds as NPY Y5 receptor antagonists |
| WO2009143178A2 (en) | 2008-05-20 | 2009-11-26 | Omeros Corporation | Pde10 inhibitors and related compositions and methods |
| TWI501965B (zh) | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物 |
| US8377930B2 (en) | 2008-08-05 | 2013-02-19 | Omeros Corporation | PDE10 inhibitors and related compositions and methods |
| MX339950B (es) * | 2010-03-12 | 2016-06-20 | Omeros Corp | Inhibidores de fosfodiesterasa 10 (pde10) y composiciones y metodos relacionados. |
| NZ630803A (en) * | 2014-04-28 | 2016-03-31 | Omeros Corp | Optically active pde10 inhibitor |
-
2014
- 2014-09-10 NZ NZ716494A patent/NZ716494A/en unknown
- 2014-09-10 NZ NZ630810A patent/NZ630810A/en unknown
-
2015
- 2015-04-24 CN CN201580023525.XA patent/CN106459026B/zh active Active
- 2015-04-24 BR BR112016025287-0A patent/BR112016025287B1/pt active IP Right Grant
- 2015-04-24 EP EP15785376.3A patent/EP3137462B1/en active Active
- 2015-04-24 KR KR1020167032983A patent/KR102496552B1/ko active Active
- 2015-04-24 RU RU2016146118A patent/RU2718863C2/ru active
- 2015-04-24 ES ES15785376T patent/ES2723437T3/es active Active
- 2015-04-24 CA CA2946756A patent/CA2946756C/en active Active
- 2015-04-24 AU AU2015253464A patent/AU2015253464B2/en active Active
- 2015-04-24 JP JP2016564031A patent/JP6474430B2/ja active Active
- 2015-04-24 US US14/696,287 patent/US9650368B2/en active Active
- 2015-04-24 WO PCT/US2015/027647 patent/WO2015167969A1/en not_active Ceased
-
2016
- 2016-10-27 IL IL248585A patent/IL248585B/en active IP Right Grant
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2017
- 2017-04-07 US US15/482,604 patent/US20180057484A1/en not_active Abandoned